1-Pentanol

1-Pentanol, (or n-pentanol, pentan-1-ol), is an alcohol with five carbon atoms and the molecular formula C5H11OH.[2] 1-Pentanol is a colourless liquid with a distinctive aroma. It is the straight-chain form of amyl alcohol, one of 8 isomers with that formula.

1-Pentanol
Skeletal formula of 1-pentanol
Ball and stick model of 1-pentanol
Names
Preferred IUPAC name
Pentan-1-ol[1]
Identifiers
3D model (JSmol)
1730975
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.684
EC Number
  • 200-752-1
25922
KEGG
MeSH n-Pentanol
RTECS number
  • SB9800000
UNII
UN number 1105
  • InChI=1S/C5H12O/c1-2-3-4-5-6/h6H,2-5H2,1H3 checkY
    Key: AMQJEAYHLZJPGS-UHFFFAOYSA-N checkY
  • CCCCCO
Properties
C5H12O
Molar mass 88.150 g·mol−1
Density 0.811 g cm−3
Melting point −78 °C; −109 °F; 195 K
Boiling point 137 to 139 °C; 278 to 282 °F; 410 to 412 K
22 g L−1
log P 1.348
Vapor pressure 200 Pa (at 20 °C)
-67.7·10−6 cm3/mol
1.409
Thermochemistry
207.45 J K−1 mol−1
258.9 J K−1 mol−1
−351.90–−351.34 kJ mol−1
−3331.19–−3330.63 kJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Warning
H226, H315, H332, H335
P261
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1
2
0
Flash point 49 °C (120 °F; 322 K)
300 °C (572 °F; 573 K)
Related compounds
Related compounds
 Hexane

Pentylamine

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

The hydroxyl group (OH) is the active site of many reactions. The ester formed from 1-pentanol and butyric acid is pentyl butyrate, which smells like apricot. The ester formed from 1-pentanol and acetic acid is amyl acetate (also called pentyl acetate), which smells like banana.

In 2014, a study was conducted comparing the performance of diesel fuel blends with various proportions of pentanol as an additive. While gaseous emissions increased with higher concentrations of pentanol, particulate emissions decreased.[3]

Pentanol can be used as a solvent for coating CDs and DVDs.

Pentanol can be prepared by fractional distillation of fusel oil. To reduce the use of fossil fuels, research is underway to develop cost-effective methods of producing (chemically identical) bio-pentanol with fermentation.[4][5]

References
  1. "n-pentanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 10 October 2011.
  2. CRC Handbook of Chemistry and Physics 65Th Ed.
  3. Wei, Liangjie & Cheung, C.s & Huang, Zuohua. (2014). Effect of n-pentanol addition on the combustion, performance and emission characteristics of a direct-injection diesel engine. Energy. 70. 10.1016/j.energy.2014.03.106.
  4. Cann, Anthony F.; Liao, James C. (2010-01-01). "Pentanol isomer synthesis in engineered microorganisms". Applied Microbiology and Biotechnology. 85 (4): 893–899. doi:10.1007/s00253-009-2262-7. ISSN 1432-0614. PMC 2804790. PMID 19859707.
  5. Tseng, Hsien-Chung (2011). Production of pentanol in metabolically engineered Escherichia coli (Thesis thesis). Massachusetts Institute of Technology. hdl:1721.1/65767.


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